Process for preparing triarylmethane dyes



Patented Aug. 12,119.30

UNITED ST E TE T P LCE ERNEST HARRY RUDD AND FRANK WILLIAM LINCH, orBLACKLEY, MAnoiass'rnn,

ENGLAND, ASSIGNORS TO BRITISH DYESTUFIES ClORIPOBATION LIMITED, OF MANCHESTER, ENGLAND PROCESS FOR PREPARING TRIARY LMET HANE No Drawing.Application filed February 2, 1928. Serial No. 251,458, and. inGreat'Britain Apri117, 1926,

In our co-pending application Serial No. 155,098, we have described aprocess for the manufacture of triaryl-carbinols which by conversioninto salts form dyestuffs, consist- 5 ing in treating atetraallryldiaminodiaryl ketone with an alkali metal and with an arylhalide. The value of this new process lies not only in the preparationof known dyestuffs by a new synthesis, but also inthe preparation ofdyestuffs obtainable with dif- Instead of chlorotoluenes, chloroxylenemay be added, similar dyestuffs being obtained. l

The present'invention relates toa process for producing 4:l-tetraalkyldiaminodiphenylaryl carbinols having the formula in which Rrepresents an alkyl group an'dR represents a xylyl group. German Patentmethod is a marked improvement over the,

German process. The present .method can produce not only compounds inwhich meta-r Xylyl residues are coupledin various positions to thecarbinol grouping-f depending upon the position substituted by thehalogen atom but also compounds in which ortho and para-Xylyl residuesare coupled to the carbinol group. J

The following example is given merely to illustrate the present methodand in no way limits the invention, as any tzifi-tetraalkyldiaminodiphenylketone and any halogen substituted Xylenemay be used in the present process.

1 Example.

of the p:p-tetramethy1diamino-diphenyl-tm-xylyl-carbinol is 145 C. Thereaction appears to take place according to the equation.

00 2N8 C1- CH:

No. 178,769, discloses a different method of producing one specificcompound of'the above general type. The method of the German patent ishoweverlimited to the production of a specific carbinol in which ameta-Xylene residue is coupled to-the carbinol grouping. By the processof the German patent it is not possible to produce compounds containingother hydrocarbon residues; not even ortho or para-xylyl residues. Thepresent 0 NaCl.

Other chloroxylenes give similar dyestuffs.

What we claim and desire to secure by Letters Patent is 1. In themanufacture of tetra-methyldiamino-diphenyl-xylyl carbinol the processwhich comprises condensing Michlers ketone with a chloroxylene. s i

In the manufacture of p p-tetramethyldiamino diphenyll-m Xylyl carbinol,the process which comprises condensing Michlers ketone with-chloro-m-xylene' in the i presence of sodium and toluene.

3. As a new product, p p-tetramethylldiamino-diphenyli-m-xyly1-carbinolhaving 5 the structural constitution and melting at 145 0., the saidp:p-tetramethyldiamino diphenyl-i-m-xylyl-carbinol being converted byacids into salts which dye 1 tanmn-mordanted cotton in bluish-greenshades.

In testimony whereof we aflix our sigma tures.

ERNEST HARRY RODD.

FRANK WILLIAM LINCI-L

